Month: May 2021

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 85953-29-3, name is Methyl 2-chloro-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H6ClFO2

Methyl(2-chloro-4-fluorophenyl)formate (134.8 g) obtained above was suspended in conc. sulfuric acid (50 ml). To the suspension, a mixture of conc. sulfuric acid (50 ml) and conc. nitric acid (50 ml) was added at about 30 C., and the mixture was stirred for 1 hour at this temperature. The reaction mixture was poured into ice-water, and precipitated crystals were collected and washed with water. Methyl(2-chloro-4-fluoro-5-nitrophenyl)formate (143 g) was thus obtained. M.P., 53-55 C.

The synthetic route of 85953-29-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US4670046; (1987); A;,
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Related Products of 106614-28-2, A common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, molecular formula is C8H6F2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 1H methyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-fluorobenzoate A mixture of EXAMPLE 1G (8.5 g), methyl 2,4-difluorobenzoate (7.05 g), and K3PO4 (9.32 g) in diglyme (40 mL) at 115 C. was stirred for 24 hours. The reaction was cooled, diluted with ether (600 mL), and washed twice with water, and brine, and concentrated. The crude product was chromatographed on silica gel with 2-50% ethyl acetatehexanes.

The synthetic route of 106614-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tao, Zhi-Fu; Wang, Xilu; Wendt, Michael; Souers, Andrew; Judd, Andrew; Kunzer, Aaron; Sullivan, Gerard; US2014/275082; (2014); A1;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 369-26-6, Computed Properties of C8H8FNO2

To the solution of compound 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (Intermediate 1) (1.26 Kg, 5.23 mol) in DMAC (15 L) was added dropwise SOCl2 (1.86 kg, 15.6 mol) at 10 °C in 30 min. To the resulting mixture warmed to 20°C was added compound methyl 3-amino-4-fluorobenzoate (884 g, 5.23 mol) in DMAC (3.0 L) over 30 min. After addition, the reaction temperature went up to 30 °C. HPLC showed the reaction went to completion within 5 min. To the reaction mixture was added water (20 L) over 20 min. The mixture was filtered and dried under vacuum to afford the title compound as a white solid; 1 H NMR (400 MHz, DMSO-d6) delta 3.87 (s, 3 H) 7.57 (dd, J=7.28, 2.01 Hz, 1 H) 7.51 (dd, J=10.16, 8.66Hz, 1 H) 7.90 (td, J=4.33, 2.38 Hz, 1 H) 8.29 (m, 2H) 8.90 (s, 1 H) 9.43 (d, J=7.53 Hz, 1 H) 10.78 (s, 1 H) Rt 6.90 mins; MS m/z 394.0 {M+H}+; Method 10 min LC

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NOVARTIS AG; BRUCE, Ian; CHAMOIN, Sylvie; COLLINGWOOD, Stephen Paul; FURET, Pascal; FURMINGER, Vikki; LEWIS, Sarah; LOREN, Jon; LV, Lin; MOLTENI, Valentina; SAUNDERS, Alex Michael; SHAW, Duncan; TURNER, Roy; YEH, Vince; WO2014/132220; (2014); A1;,
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Synthetic Route of 59833-69-1,Some common heterocyclic compound, 59833-69-1, name is Methyl 2-(3-amino-4-chlorophenyl)acetate, molecular formula is C9H10ClNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a stirred solution of 12e (62 mg, 0.4 mmol) in CH2Cl2 (5 mL) were added a solution of 18 (133 mg, 0.4 mmol) in CH2Cl2 (3 mL) and then pyridine (0.067 mL, 0.8 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with water and extracted with EtOAc (×2). The combined organic layers were washed with 1 M NaOH aq, water, brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (120 mg, 63%); TLC Rf = 0.14 (n-hexane/EtOAc, 7:3); 1H NMR (300 MHz, CDCl3) delta 7.60-7.38 (m, 4H), 7.32 (t, J = 7.8 Hz, 1H), 7.06 (d, J = 7.5 Hz, 1H), 6.92-6.77 (m, 4H), 6.74-6.66 (m, 2H), 4.70-4.60 (m, 1H), 4.26 (dd, J = 9.6, 5.4 Hz, 1H), 4.14 (dd, J = 11.4, 6.6 Hz, 1H), 3.71 (s, 3H), 3.65 (s, 2H), 3.39 (dd, J = 11.4, 3.0 Hz, 1H), 3.26 (dd, J = 11.4, 7.8 Hz, 1H), 2.91 (s, 3H), 2.51 (s, 3H).CommentTo a stirred solution of methyl ester (120 mg, 0.25 mmol) described above in MeOH (4 mL) and THF (4 mL) was added 5 M NaOH aq (2 mL). After stirring for 1 h at room temperature, the reaction mixture was diluted with 2 M HCl aq and extracted with EtOAc (×2). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to give a crude product, which was washed with EtOAc/n-hexane to yield 4a (85 mg, 73%) as a pale blue powder

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-(3-amino-4-chlorophenyl)acetate, its application will become more common.

Reference:
Article; Iwahashi, Maki; Takahashi, Eiji; Tanaka, Motoyuki; Matsunaga, Yoko; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5361 – 5371;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 1-bromocyclobutanecarboxylate

A) Ethyl 1-azidocyclobutane-1 -carboxylate: To a flask was added ethyl 1-bromocyclobutane-1-carboxylate (5.0 g, 25 mmol), dimethylformamide (120 mL), and sodium azide (2.43 g, 37.5 mmol). After stirring at room temperature for 2 days, the reaction was taken up in ether and washed with water (3 x 150 mL). The organic layer was removed and dried over magnesium sulfate. The drying reagent was removed by vacuum filtration and the solvent removed by rotary evaporator to give a colorless liquid, 3.69 g, yield 87%. 1H-NMR (CDCl3) delta 1.29 (t, 3H), 2.00 (m, 2H), 2.25 (m, 2H), 2.55 (m, 2H), 4.22 (q, 2H); IR (neat) 2109 cm-1.

The synthetic route of 35120-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Products Inc.; EP952148; (1999); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

4891-38-7, name is Methyl Phenylpropiolate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: esters-buliding-blocks

1.0 mmol (123.1 mg) of m-methoxyaniline and 1.0 mmol (160.2 mg) of methyl phenylpropiolate and1.2 mmol (122.4 mg) of phenylacetylene and0.005 mmol (1.8 mmol) of Cu (OTf)2catalystmg), HOTf 0.01mmol(1.5mg), a nitrile solvent has 2mL, deg.] C for 8h at 100 oil bath, cooled to room temperature, water was added 5mL, extracted with ethyl acetate threetimes, the organic layers were combined, concentrated under reduced pressure, the product after Purification by column chromatography, silica gel 300-400 mesh, eluantmixtureof ethyl acetate andpetroleum ether, the volume ratio of 1: 5, to obtain a white solid product 296.4mg, 95% yield, purity 99.9%

The synthetic route of 4891-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanyang Normal College; Zhang Xu; Xu Xuefeng; (13 pag.)CN106380463; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, A new synthetic method of this compound is introduced below., Computed Properties of C11H13NO2

EXAMPLE 5 5-(2,5-dimethylphenoxy)-2,2-dimethylvaleric acid (6.25 g) is converted to the corresponding acid chloride by the action of oxalyl chloride as in the Example 1. The above acid chloride is dissolved in THF (60 ml) and is added to a solution of ethyl 4-aminocinnamate (4.7 g) in THF (60 ml) containing Et3 N (2.5 g) at ambient temperature followed by stirring overnight. The inorganic solid is filtered off and the filtrate is evaporated to dryness to yield 9.5 g of the product ethyl 3-[4-[[5-(2,5-dimethylphenoxy)-2,2-dimethyl-1-oxopentyl]amino]phenyl]-2-propenoate; mp 101°-102° C. following crystallization from isopropyl ether.

The synthetic route of 5048-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4413011; (1983); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 653-92-9,Some common heterocyclic compound, 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, molecular formula is C8H6BrFO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of (2) in 1 ,4-dioxane (4 mL) were added 1 ‘1 [bis(diphenylphosphino) ferrocene] dichloropalladium(ll) (0.2 eq), Na2C03 (8 eq) and one of the following regents heteroarylboronic acid or heteroaryiboronic acid pinacol ester or heteroarylboronic MIDA ester (2 eq) in a microwave tube. After addition of H20 (1 mL), the tube was sealed and the reaction mixture was stirred at 90C for 16 h. The mixture was allowed to cool to room temperature, was filtered through celite and MgS04 and the filter was repeatedly washed with ethyl acetate. After removing the solvent under reduced pressure, the crude residue was dissolved in saturated aqueous Na2C03 solution. The aqueous layer was extracted three times with CHCI3 and the combined organic layers were washed with saturated, aqueous NaCI solution and dried over Na2S04). The organic solvent was removed under reduced pressure and the residue was purified by preparative HPLC to obtain the appropriate target compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromo-4-fluorobenzoate, its application will become more common.

Reference:
Patent; FRIEDRICH-ALEXANDER-UNIVERSITAeT ERLANGEN-NUeRNBERG; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BANERJEE, Ashutosh; BARTUSCHAT, Amelie; EITEL, Katrin; GMEINER, Peter; HEINRICH, Markus; HOFMANN, Josefa; HUeBNER, Harald; RAMPP, Hannelore; SCHAAKE, Benjamin; KOBILKA, Brian; SUNAHARA, Roger; CLARK, Mary Joyce; FISH, Inbar; SHOICHET, Brian; (90 pag.)WO2019/110521; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1459-96-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1459-96-7 name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate A51A: 4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid To a solution of dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate (0.92 g, 4.07 mmol) in MeOH (5 mL) was added LiOH (0.102 g, 4.27 mmol) in water (4 mL) at RT. The reaction mixture was heated at 65 C. for 6 h. It was then cooled to RT and concentrated. The residue was acidified with 1N HCl to pH ?2. The solid (presumed side product diacid) was removed by filtration. The filtrate was extracted with EtOAc, and the combined organic layer was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated to afford Intermediate A51A as a white solid, which was used for the next step without further purification. MS(ES): m/z=213 [M+H]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 12.11 (s, 1H), 3.66 (s, 3H), 1.78-1.58 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

A solution of sodium hydroxide (2.85 g, 71.3 mmol) in water (3 ml) was added to a stirred solution of diethyl oxaloacetate sodium salt (8.7 g, 50 mmol) in water (50 ml) and the mixture stirred for 20 minutes. Cyclopropylcarboxamidine hydrochloride salt (5.0 g, 40 mmol) was added to the solution and the mixture was heated at 70 0C overnight, then cooled to ambient temperature and acidified to pH1 by the cautious addition of concentrated hydrochloric acid. The precipitate was isolated by filtration and dried to yield 2-cyclopropyl-4-hydroxypyrimidine-6-carboxylic acid (4.7 g, 63%). 1H nmr (400MHz, d6-DMSO) deltaH 13.30 (1 H, br s), 12.97 (1 H, br s), 6.59 (1 H, s), 1.94 (1 H, quintet), 1.04 (4H, m) ppm.

The synthetic route of 40876-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA LIMITED; SYNGENTA PARTICIPATIONS AG; WHITTINGHAM, William, Guy; WINN, Caroline, Louise; GLITHRO, Harry; BOUSSEMGHOUNE, Mohamed, Abdelouahab; ASPINALL, Mary, Bernadette; WO2010/92339; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics